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Hydrochloric Acid → Tert-butyl 7-(3,4-dichlorophenyl)-7-(hydroxymethyl)-6-oxo-1,4-oxazepane-4-carboxylate

HRID 1022828
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1022828
[OH-:1].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:8][C:9]=1[Cl:10].[CH2:26]=O.Cl>C(O)C.CS(C)=O.[Cl-].[Na+].O>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([CH2:26][OH:1])[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:8][C:9]=1[Cl:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 66976649HCID 66976649, Verbindung

Produkt 1

HCID 66976886Tert-butyl 7-(3,4-dichlorophenyl)-7-(hydroxymethyl)-6-oxo-1,4-oxazepane-4-carboxylateAusbeute 456,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 702EthanolLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Potassium hydroxide (40 mg) was dissolved in ethanol (1.25 ml), and the solution was diluted with DMSO (25 mL). To this solution were added tert-butyl 7-(3,4-dichlorophenyl)-6-oxo-1,4-oxazepane-4-carboxylate (2.60 g) and paraformaldehyde (267 mg), and the mixture was stirred at room temperature for 30 min. The reaction solution was neutralized with 1 N hydrochloric acid, brine was added, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.27 g).

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed twice with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2a60eb57a36b403b8f0a817f4aac6a6e
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722662B2

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